Journal of Olly Headey. Co-founder & CTO at FreeAgent

The Flaming Lips – American Head

Many (21!) years ago, when I was in the mood for relaxing to some spaced-out dream rock I’d listen to Spiritualized or The Soft Bulletin by far out American odd-band, The Flaming Lips. They were wonderful albums. The follow up to The Soft Bulletin was Yoshimi Battles The Pink Robots, which was the band’s big commercial success, although for me it wasn’t quite up there with Bulletin. From these giddy, world conquering heights it all seemed to tumble downhill for them rather quickly and despite releasing 12 albums since, none of them ever hit the mark for me (or the professional critics).

The Lips’ 16th album, American Head was released this week and I decided to give it a listen, and I’m so glad I did! Some might call it pastiche, but I don’t care. Not for me. It’s a band returning to their roots. It has the same blissed out vibes as their earlier classics and it’s a total delight to listen to.

Finally 2020 has something to show for itself.

Why you need to run all-hands meetings

A typical all-hands meeting : Photo @byfoul

We’ve been told that culture eats strategy for breakfast, and organisational health trumps everything else in business and I wouldn’t disagree. Strong teamwork and effective communication are the best ways to build trust, and trust is at the heart of every successful team.

As a leader in a fast-growing company, one ceremony I’ve found crucial for encouraging effective communication is a weekly ‘all-hands’ meeting. This is an hour where everyone across the team congregates to share plans, ideas, stories. It’s a place for sharing, to improve awareness, reinforce values and to help develop an inclusive culture which ultimately results in stronger trust. Every company should do this!

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Using SWOT analysis to develop your engineering strategy

Photo by @jamietempleton

Your first 90 days in a new leadership role (in particular, a VP Engineering or CTO role) will be largely spent in orientation. You’ll be getting to know the ways and hows of the business in detail: its culture, its values, its structure, its current priorities, the things that work well and, of course, the things that don’t. You need to see warts and all, leaving no stone unturned.

A big investment of time will be getting to know your peers on the exec team (your first team): what makes them tick, what are their strengths, what skills are they working on (“weaknesses”), what are their frustrations, what are their interests. Similarly, you’ll be getting to know the people you’re managing as direct reports. First impression count. On both sides.

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👋 vs Fastmail. A review.

I’ve been a fanboy of DHH and Jason of Basecamp since around 2006 when I first read Getting Real and started writing code in Rails. We used Basecamp (and for a brief time, Highrise) as our primary communication tool for the first few years of FreeAgent and it was a big influence from a product point of view. For the past 8 years though, I’ve not really used Basecamp products but I have remained a follower of the company and founders, reading their books and enjoying their Twitter rants. I’m still an ardent Rails fan as well 👨‍💻

When I heard about HEY, I was immediately interested. Not because I’ve lost control of my inbox (I’m an order-freak and avid filterer so my inbox is generally a tranquil place), but because the HEY statement about why “Email’s a treasure” rang so true to me and because a brand-new, Rails-based, Basecamp product is always going to be pretty exciting to try.

I got my invite early and I’ve been kicking the tyres for a while, so I’ve written up a few thoughts to get them out there and to hear about what other people think.

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Locked In The House (Vol. 1)

Once upon a time I used to buy vinyl records and play them in dark rooms full (sometimes) of people. I used to record mixes to C90 cassette (!), and eventually on CD, and I’d design covers and send them to willing listeners I met on obscure internet mailing lists in the 1990s. They were halcyon days ☀️

I flogged my decks and mixer in 2011 and haven’t bought vinyl since the mid-00s (I still have all my records in the garage though, if anyone wants them?). I do miss it a bit, but life moves on.

I still love the music though and my tastes in ‘dance’ music haven’t really changed that much. The music might be similar but the technology has moved on enormously. I can now instantly buy tracks in lossless digital format for a fraction of what I’d pay for vinyl even a decade ago, and I can mix them up with nothing more than an iPad and the Traktor DJ app which, while not quite a substitute for the tactile 1200s experience, is still remarkably satisfying.

At the start of lockdown I bought a bag of tracks from Juno Download and threw a new mix together.

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2019 was a blur

Years now fly by. 2019 feels more of a blur than any previous year, which is probably the ageing process. Some great highs this year, but sadly some deep, dark lows. 2019 was definitely a year where I’ve felt like there’s been a lack of ‘thinking time’, but despite that I always seem to do enough to pull together an annual cultural highlight list.

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How to Eat a Burrito

On stage at Turing 2019

I was privileged to be able to speak at the Turing Fest conference in my home town of Edinburgh today. It’s a “cross-functional tech conference” covering everything from marketing, sales, engineering, startups and business growth. I’ve been every year for the past three (or perhaps it’s four) years and it’s always been excellent. It’s great to see such a high quality conference in Edinburgh, it’s up there with the world’s best.

The calibre of talks is generally really high, so I put in what felt like an inordinate amount of time preparing the talk. Partly this was because I really didn’t want to cock it up, but largely because it turns out preparing a well-rehearsed talk - even a 30 minute one – is a mightily time-consuming thing to do! I really enjoyed the whole process – even delivering the talk was fun, if slightly surreal – but my respect for the speakers has gone through the roof now that I can properly appreciate the amount of time and sheer effort they devote to putting together their presentations.

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Time Well Spent

A question that’s always worth asking yourself: is the time I’m spending doing a particular task or activity well spent? Is it adding value to you or to your business in some way? Before you start work on something, ask yourself the question. In the middle of working on something, pause and ask yourself the question. When you’ve left a meeting, reflect and ask yourself the question. Was it time well spent? If it wasn’t, try and make a change.

Meetings, especially infinitely recurring ones, are a really good test of time well spent. Meetings are typically scheduled for a minimum of 30 minutes, but more often for 60 minutes simply because that’s what Google or Microsoft have decided is the correct default. Parkinson’s Law means that these meetings will last as long as they’re scheduled for, irrespective of whether that is time well spent. It’s probably true that most meetings are not time well spent. You can change that by running better meetings, or by not holding them in the first place. There are alternative and arguably less disruptive ways to share information and make decisions.

It’s not just meetings. It’s all too easy in our hyper-connected, always-on world to spend your time doing routine work, or tasks, that ultimately have no major benefit. Slack want you to be in Slack all day but there’s no difference between being in Slack to being in Facebook or Twitter or LinkedIn all day. You’re just scrolling, channel surfing, waiting for that next dopamine hit – that “interesting article”, that hedgehog gif or an @here that, frankly, can wait until tomorrow. Or the next day. It’s a procrastination drug, a day-long meeting that everyone is participating in. Try turning it off for a while, consume in digests and try and ignore the FOMO.

Just don’t be too hard on yourself. I’ve been writing for twenty minutes and I’m now questioning the value. On reflection the writing practice is good, and maybe the three readers of this blog will take something useful away from the two minutes they spent reading it. I’m calling it time well spent.

Can I check Twitter now?

So long, 2018

I always get this feeling of gritty ambition at the start of a new year. Those pre-Christmas months, from the start of autumn through to winter take their toll, and while Christmas is a special time of year, for us it’s usually hectic in one way or another so not exactly conducive to relaxation. Those quiet days between Hogmanay and back to work/school are when I finally feel I have time to relax, reflect and re-energise. It’s this state of mind, free of hurry and stress, that seems to result in a surge in creative ideas for me. I imagine it’s the same for many people, hence all the ‘year in review’ lists and eager self-improvement resolutions. It feels good to set goals… when you’re up for taking them on.

Renovation photo

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